The issue just seems to be that the process is dying before Visual Studio can 
properly attach. Ivan, try using " System::Diagnostics::Debug.assert false" 
which will pop up a dialog box, thus blocking the thread, but without using the 
"int 3" x86 instruction as System::Diagnostics::Debugger.break would. The 
latter might cause some issues. 

Also, could there be any issue with the fact that ASP.Net is running a service? 
Some dialog boxes might be getting hidden since services run in their own 
hidden workspace/workstation (I think)

-----Original Message-----
From: ironruby-core-boun...@rubyforge.org 
[mailto:ironruby-core-boun...@rubyforge.org] On Behalf Of Cory Foy
Sent: Sunday, March 14, 2010 11:25 PM
To: ironruby-core@rubyforge.org
Subject: Re: [Ironruby-core] IronRuby.Rack how to debug?

Ivan Porto Carrero wrote:
> I am unable to debug the application though. If I put
> System::Diagnostics::Debugger.break somewhere it will correctly break there
> but eventually visual studio (2008 and 2010) will just get tired of it and
> claim they have to quit.  I've seen that the debug windows gives me a lot of
> information and I was hoping that there would be some useful information
> there for me but because visual studio quits right at the interesting moment
> I'm unable to figure out what's going on as nothing is printed in the
> sysinternals debugvw application.

You may also want to try WinDBG with the SOS extension. Here's slides 
with code and examples on using WinDBG to debug .NET applications:

http://www.slideshare.net/CoryFoy/debugging-net-applications-with-windbg

What I'd try is using the File menu to attach to the process, then when 
it breaks typing in ".loadby sos mscorwks". Next type in "sxe clr" and 
then "g". It will now break on all CLR exceptions. You can type 
"!printexception" to see the exception details when it breaks, and "g" 
to make it go again. You can also type "!help" to see all of the SOS 
commands.

-- 
Cory Foy
http://www.coryfoy.com
http://twitter.com/cory_foy
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